Trifluoroacetic acid methylene chloride → 2H-1,4-Benzoxazin-3(4H)-one, 4-(4-piperidinyl)-

HRID 967410Notes

Reaction equation

HRID 967410 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[O:17][CH2:16][C:15]2=[O:24])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>CCOCC>[NH:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[O:17][CH2:16][C:15]2=[O:24])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 223806764-(3-Oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 222938102H-1,4-Benzoxazin-3(4H)-one, 4-(4-piperidinyl)-Yield 135.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-(3-Oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester (17 g, 51 mmol) and 1:1 TFA/CH2Cl2 (40 mL) were combined and set stirring. After 45 min the mixture was evaporated to give a clear brown oil. The oil was set stirring and Et2O was added (300 mL). A solid formed and was filtered, washed with Et2O and air dried to give 16 g (90%) of a light beige solid. MS (electrospray): exact mass calculated for C13H16N2O2, 232.12. m/z found, 233.1 [M+H]+. 1H NMR (400 MHz, CD3OD): 7.44 (dd, J=6.5, 1.4 Hz, 1H), 7.20-7.7.10 (m, 3H), 4.58 (s, 2H), 4.55-4.45 (m, 1H), 4.65-4.55 (m, 2H), 3.27 (dt, J=13.0, 2.3 Hz, 2H), 3.05 (dd, J=12.3, 4.1 Hz, 2H), 2.15 (d, J=13.8 Hz, 2H).

Workup

  1. customAfter 45 min the mixture was evaporated
  2. customto give a clear brown oil
  3. stirringThe oil was set stirring
  4. customA solid formed
  5. filtrationwas filtered
  6. washwashed with Et2O and air
  7. customdried

Sources & evidence

ORD record
ord-4838c846ca3348dbb11b2199d1be8247
Source dataset
uspto-grants-2005_10
Patent number
US06953793B2

Reaction notes

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